Whether you’re at a neighborhood party or around the dinner table, you want to start a conversation that doesn’t quickly sputter out. As everyone knows, if you ask, “How was your day?” you’re bound to get a quick “fine” … or a grunt, if you dare chat up your teen. Truth is, almost everyone feels awkward about making small talk, so we default to stock questions, which inevitably lead to canned answers. Yawn.
But it’s surprisingly easy to level up your chit-chat: We rounded up interesting questions to ask when you want to encourage off-the-cuff sharing. These upgraded questions work as icebreakers to help you connect more with people you don’t know very well and as prompts to spark meatier conversations with friends and family (yes, high school-aged spawn included!).
One quick tip: If the person you’re chatting up isn’t rushing to respond to a question, jump up in and answer it yourself—this will make them feel more comfortable opening up too. OK, ready to back-and-forth like a boss? Pick and choose from the following interesting questions to ask your family, friends and work friends. You’ll get to know them on a whole new, utterly fascinating level.
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Instead of asking “How are you?” ask…
- What’s the best thing that happened to you today?
- What are you most looking forward to this week?
- What’s the last thing that made you laugh out loud?
- What do you do for fun that you suspect most people would find boring?
- Which emoji sums up your week?
- What’s been on your mind recently?
- If you got a do-over, what would you do differently this month? This year?
- On a scale of 1 to 10—with 10 being the best—what’s your current state of mind?
- What is the last thing you toasted to?
- What’s something that really happened to you that people find hard to believe?
- What’s a risk you wish you’d taken?
- What’s your go-to way to unwind?
- What word describes your life right now, and why?
- Who or what always cheers you up?
Instead of asking “How was your day?” ask…
- What made you smile today?
- What did you listen to on the way over here?
- Did anything make you roll your eyes today?
- What is the weirdest thing you saw on your commute?
- What talent would have come in handy today?
- What was the nicest surprise you got in the past 24 hours?
- Is there anything you did today that you’d love to do every day?
- Which song would be the perfect theme for your day?
- If your day were a movie, who would play you?
- What is your current unpopular opinion?
- Who made your day easier today?
- What’s one way you aim to make tomorrow better than today?
Instead of asking “What’s new?” ask…
- Do you have any fun trips planned?
- What podcast are you currently obsessed with?
- What new movie or TV show should I check out? Which one is overrated?
- What could you give a TED Talk on with zero prep?
- Have you discovered any hilarious TikToks I should know about?
- What are the most surprising facts you’ve heard lately?
- What is the best purchase you’ve made all year?
- What is the one thing you most regret buying?
- Which band or musician have you recently rediscovered?
- What have you tried recently that you’d never do again?
- What is one thing you have on you at all times?
- What are you most looking forward to this year?
- How have things changed for you since we last spoke?
Instead of asking your kids “How was school?” ask…
- What was the best thing that happened in school today?
- What were you most proud of today?
- What was the most surprising thing you learned today?
- Who had the best snack at lunch?
- Who did you help today? Who helped you?
- Which class made you most excited to learn, and why?
- When did you feel the most bored?
- If you could swap seats with anyone in your class, who would you pick, and why?
- What was the hardest thing you did today?
- If you could give your teacher one suggestion, what would it be?
- What made you laugh the most today?
- What is something you know now that you didn’t know yesterday?
Instead of asking “How’s work going?” ask…
- What is an exciting project you’re tackling?
- What is one new thing you’d love to try?
- You schedule a team Zoom: cameras on or off?
- Describe your go-to work outfit these days.
- What did you want to be when you grew up?
- What is your best piece of advice for a college grad entering your field now?
- What is your office superpower?
- What is a deal-breaker in a boss?
- What’s your best idea for a side hustle?
- If you could do your job from anywhere on the planet for three months, where would you jet off to?
- What is the nicest work compliment you’ve ever received?
- How do you power through a mid-afternoon slump?
- Are you happy in your career?
- How do you feel about mental health days: legit or lazy?
- What would you like to be celebrating in one year? Five years?
Instead of asking “What’s on your mind?” ask…
- What was your most embarrassing moment?
- Which conspiracy theory could you almost buy into?
- What is your biggest regret?
- Was there ever a time when you broke the rules and it turned out to be the best decision ever?
- What is topping your bucket list these days?
- Who is the most famous person you’ve ever met?
- What is your personal motto to live by?
- What was the bravest thing you ever did?
- If you had to give your 18-year-old self one piece of advice, what would it be?
- What do you eat when nobody is around?
- Assuming cost is no object, where would you like to travel next?
- What keeps you up at night?
- If you could time-travel to one decade in the past, which era would you choose?
- What’s one subject you’d like to learn more about if you had the time?
Why trust us
For over 100 years, Reader’s Digest has explored the nuances of relationships, working with such luminaries as Dr. Ruth Westheimer, John Gottman, PhD, and Leo Buscaglia (“Dr. Love”). We ran a decade-long relationships column and have published a compendium of features, Love and Marriage: The Reader’s Digest Guide to Intimate Relationships. For this piece on interesting questions to ask, Lisa Lombardi tapped her experience as a longtime journalist to ensure that all information is accurate and offers the best possible advice to readers. We support this information with credentialed experts and primary sources such as government and professional organizations, peer-reviewed journals and our writers’ personal experiences where it enhances the topic. We verify all facts and data and revisit them over time to ensure they remain accurate and up to date. Read more about our team, our contributors and our editorial policies.
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